N-(3-Aminopropyl)morpholine → HCID 69482546, compound

HRID 2364255Notes

Reaction equation

HRID 2364255 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([OH:26])=[C:15]([C:21](OCC)=[O:22])[C:16](=[O:20])[NH:17]2)=[N:12][CH:11]=1.[NH2:27][CH2:28][CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([OH:26])=[C:15]([C:21]([NH:27][CH2:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[O:22])[C:16](=[O:20])[NH:17]2)=[N:12][CH:11]=1

Participants

3

Reactant 2

HCID 61055N-(3-Aminopropyl)morpholineHCID 69480228HCID 69480228, compound

Product 1

HCID 69482546HCID 69482546, compound

Procedure

This compound was prepared from ethyl 7-[(2,4-difluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 4-(3-aminopropyl)morpholine employing methods similar to those described in Example 2 and was obtained as a white solid: 1H NMR (d6-DMSO) tautomers are observed δ 11.75 (1H, br s), 10.7 (1H, br s), 10.20 (1H, br s), 8.17 (0.45H, s), 8.15 (0.55H, s), 7.45-7.21 (3H, m), 7.10-7.04 (1H, m), 4.02 (2H, s), 3.56-3.51 (4H, m), 3.31-3.24 (2H, m), 2.48-2.32 (6H, m), 1.65-1.61 (2H, m); HRMS calcd for C23H24F2N4O4+H+: 459.1844. Found 459.1856.

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-4ad28356f191464f9de3b1869f2d0e63
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…